La Trobe

Lewis acid activation of Weiss' reagents ([PhI(Pyr)2]2+) with boranes and isolation of [PhI(4-DMAP)]2+

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posted on 2025-02-04, 04:28 authored by Aseel Bakro, Lachlan Sharp-Bucknall, Tiffany Poynder, Jack K. Clegg, David WilsonDavid Wilson, Jason DuttonJason Dutton

Abstraction of a pyridine ligand from Weiss' reagent ([PhI(Pyr)2]2+) using BF3-Et2O was found to activate Weiss' reagent towards electrophilic aromatic substitution reactions. The activated species can be isolated when 4-DMAP is used as the pyridine ligand and was determined to be [PhI(4-DMAP)]2+ in solution. The isolated cation was reactive in electrophilic aromatic substitution reactions towards mesitylene, xylene and toluene that Weiss' reagent itself does not react with.

Funding

La Trobe University and the Australian Research Council (FT16010007, DP200100013).

History

Publication Date

2021-11-25

Journal

Chemical Communications

Volume

57

Issue

91

Pagination

12163-12166

Publisher

The Royal Society of Chemistry

ISSN

1359-7345

Rights Statement

© The Royal Society of Chemistry 2021. This is the Accepted Version.

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